Polymerizable compound and optically anisotropic body

Abstract

The polymerizable liquid crystal compound has reverse wavelength dispersion or low wavelength dispersion and has high solubility in various solvents. The polymerizable liquid crystal compound provides an optically anisotropic body having high adhesiveness to substrates (or alignment films), by adding the polymerizable liquid crystal compound to a polymerizable composition and polymerizing the polymerizable composition using ultraviolet light. The invention provides a polymerizable composition containing the polymerizable liquid crystal compound having reverse wavelength dispersion or low wavelength dispersion, a polymer obtained by polymerizing the polymerizable composition, and an optically anisotropic body using the polymer. The present invention provides a polymerizable low wavelength dispersion or polymerizable reverse wavelength dispersion compound having in the molecule a partial structure represented by the general formula (AO-1); and also provides a composition containing the compound, a polymer obtained by polymerizing the composition, and an optically anisotropic body and the like using the polymer.

The invention claimed is: 
     
       1. A polymerizable low wavelength dispersion or polymerizable reverse wavelength dispersion compound having a partial structure represented by the following general formula (AO-1) in a molecule: 
       
         
           
           
               
               
           
         
         wherein n 0  represents an integer of 2 or more; and R 0  represents a linear alkylene group having 2 to 20 carbon atoms, a branched alkylene group having 3 to 20 carbon atoms, an arbitrary hydrogen atom in the alkylene group may be substituted with a fluorine atom or a chlorine atom, and plural les may be the same or different, 
         wherein the compound has, in a molecule, at least one group represented by the following general formula (I-0-R): 
       
       
         
           
           
               
               
           
         
         wherein P 0  represents a polymerizable group; k 0  represents an integer of 1 to 10; Sp 0  represents a linear alkylene group having 1 to 30 carbon atoms, a branched alkylene group having 3 to 30 carbon atoms, or a single bond, one —CH 2 — or two or more (—CH 2 —)'s not adjacent to each other in the alkylene group may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, or —C≡C, and plural Sp 0 's, if any, may be the same or different; and (Sp 0 ) k0  may be a group having a partial structure represented by the general formula (AO-1), provided that P 0 —(Sp 0 ) k0 —contains no —O—O— bond, 
         wherein the compound is represented by the general formula (I): 
       
       
         
           
           
               
               
           
         
         wherein R 1  is the group represented by the general formula (I-0-R) in which)(Sp 0 ) k0  includes the partial structure represented by the general formula (AO-1), and 
         wherein R 2  represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a cyano group, a nitro group, an isocyano group, a thioisocyano group, a linear alkyl group having 1 to 20 carbon atoms or a branched alkyl group having 3 to 20 carbon atoms, in which arbitrary hydrogen atoms in the group may be substituted with a fluorine atom and one —CH 2 — or two or more (—CH 2 —)'s not adjacent to each other may be each independently substituted with —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—, —CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —N═N—, or —CH═N—N═CH—; 
         A 1  and A 2  each independently represent a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or 1,3-dioxane-2,5-diyl group, these groups may be unsubstituted or substituted with one or more substituents L's, L represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, a linear alkyl group having 1 to 20 carbon atoms or a branched alkyl group having 3 to 20 carbon atoms, in which one —CH 2 — or two or more (—CH 2 —)'s not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH— or —NH—CO—, and an arbitrary hydrogen atom in the alkyl group may be substituted with a fluorine atom, and plural L's in the compound, if any, may be the same or different; 
         Z 1  and Z 2  each independently represent —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF≡CF—, —C≡C—, or a single bond, plural Z 1 's, if any, may be the same or different, and plural Z 2 's, if any, may be the same or different; 
         G 1  represents a divalent group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heteroring, the number of π electrons contained in the aromatic ring(s) in the group represented by G 1  is 12 or more, and the group represented by G 1  may be unsubstituted or substituted with one or more substituents L G 's, L G  represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, a linear alkyl group having 1 to 20 carbon atoms or a branched alkyl group having 3 to 20 carbon atoms, in which one —CH 2 — or two or more (—CH 2 —)'s not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and an arbitrary hydrogen atom in the alkyl group may be substituted with a fluorine atom, or L G  may represent a group represented by P LG —(Sp LG —X LG ) kLG — where P LG  represents a polymerizable group, Sp LG  represents a linear alkylene group having 1 to 10 carbon atoms in which one —CH 2 — or two or more (—CH 2 —)'s not adjacent to each other may be each independently substituted with —O—, —COO—, or —OCO— or a single bond, plural Sp LG 's, if any, may be the same or different, X LG  represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, plural X LG 's, if any, may be the same or different, and kLG represents an integer of 0 to 10, and plural L G 's in the compound, if any, may be the same or different; and 
         m1 and m2 each independently represent an integer of 0 to 6, provided that m1+m2 is an integer of 0 to 6; 
         provided that the general formula (I) contains no —O—O— bond, 
         wherein in the general formula (I), G 1  represents a group selected from the following general formulae (M-1) to (M-6): 
       
       
         
           
           
               
               
           
         
         wherein these groups may be unsubstituted or substituted with one or more substituents L G 's as described above; arbitrary (—CH═)'s may be each independently substituted with —N═; (—CH 2 —)'s each independently represent —O—, —S—, —NR T —, wherein R T  represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, —CS—, or —CO—; T 1  represents a group selected from the following formulae (T1-1) to (T1-6): 
       
       
         
           
           
               
               
           
         
         wherein these groups may have a bonding at an arbitrary position, arbitrary (—CH═)'s may be each independently substituted with —N═, (—CH 2 —)'s each independently represent —O—, —S—, —NR T —, wherein R T  represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS—, or —CO—, and these groups may be unsubstituted or substituted with one or more substituents L G 's as described above, or a group selected from the general formulae (M-7) to (M-14): 
       
       
         
           
           
               
               
           
         
         wherein these groups may be unsubstituted or substituted with one or more substituents L G 's as described above, arbitrary (—CH═)'s may be each independently substituted with —N═, (—CH 2 —)'s each independently represent —O—, —S—, —NR T — wherein R T  represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, —CS—, or —CO—; and T 2  represents a group selected from the following general formula (T2-1) or (T2-2): 
       
       
         
           
           
               
               
           
         
         wherein W 1  represents a group having 1 to 40 carbon atoms and containing an aromatic group and/or a nonaromatic group which may be substituted, the aromatic group may be a hydrocarbon ring or a heteroring, and the nonaromatic group may be a hydrocarbon group or a hydrocarbon group in which an arbitrary carbon atom is substituted with a heteroatom provided that oxygen atoms do not directly bind to each other; 
         W 2  represents a hydrogen atom, a linear alkyl group having 1 to 20 carbon atoms or a branched alkyl group having 3 to 20 carbon atoms, in which one —CH 2 — or two or more (—CH 2 —)'s not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and an arbitrary hydrogen atom in the alkyl group may be substituted with a fluorine atom, or W 2  may represent a group having 2 to 30 carbon atoms and having at least one aromatic group, and the group may be unsubstituted or substituted with one or more substituents L W 's, or W 2  may represent a group represented by P W —(Sp W —X W ) kW — where P W  represents a polymerizable group, Sp W  represents a linear alkylene group having 1 to 30 carbon atoms, a branched alkylene group having 1 to 30 carbon atoms, or a single bond, one —CH 2 — or two or more (—CH 2 —)'s not adjacent to each other in the alkylene group may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, or —C≡C, and plural Sp W 's, if any, may be the same or different, X W  represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, plural X W 's, if any, may be the same or different, and kW represents an integer of 0 to 10, and L W  represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, a linear alkyl group having 1 to 20 carbon atoms or a branched alkyl group having 3 to 20 carbon atoms, in which one —CH 2 — or two or more (—CH 2 —)'s not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and an arbitrary hydrogen atom in the alkyl group may be substituted with a fluorine atom, or L W  may represent a group represented by P LW —(Sp LW —X LW ) kLW — where P LW  represents a polymerizable group, Sp LW  represents a linear alkylene group having 1 to 10 carbon atoms in which one —CH 2 — or two or more (—CH 2 —)'s not adjacent to each other may be each independently substituted with —O—, —COO—, or —OCO— or a single bond, plural Sp LW 's, if any, may be the same or different, X LW  represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, plural X LW 's, if any, may be the same or different, and kLW represents an integer of 0 to 10, and plural L W 's in the compound, if any, may be the same or different; 
         Y represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, a linear alkyl group having 1 to 20 carbon atoms or a branched alkyl group having 3 to 20 carbon atoms, in which one —CH 2 — or two or more (—CH 2 —)'s not adjacent to each other may be each independently substituted with —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —CH═CH—, —CF═CF—, or —C≡C—, and an arbitrary hydrogen atom in the alkyl group may be substituted with a fluorine atom, or Y may represent a group represented by P Y —(Sp Y —X Y ) kY — where P Y  represents a polymerizable group, Sp Y  represents a linear alkylene group having 1 to 10 carbon atoms in which one —CH 2 — or two or more (—CH 2 —)'s not adjacent to each other may be each independently substituted with —O—, —COO—, or —OCO— or a single bond, plural Sp Y 's, if any, may be the same or different, X Y  represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —OCO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 —, —OCO—CH 2 —, —CH 2 —COO—, —CH 2 —OCO—, —CH═CH—, —N═N—, —CH═N—N═CH—, —CF═CF—, —C≡C—, or a single bond, plural X Y 's, if any, may be the same or different, and kY represents an integer of 0 to 10; and 
         W 1  and W 2  may be linked together to form a ring structure. 
       
     
     
       2. The compound according to  claim 1 , wherein in the general formula (I-0-R), P 0  represents a group selected from the following formulae (P-1) to (P-14) and (P-16) to (P-20): 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
       3. The compound according to  claim 1 , wherein W 2  in the general formula (T2-1) or the general formula (T2-2) comprises a partial structure represented by the general formula (AO-1). 
     
     
       4. The compound according to  claim 1 , wherein in the general formula (I), G 1  is represented by the formula (M-7) or (M-8). 
     
     
       5. A composition comprising the compound of  claim 1 . 
     
     
       6. A liquid crystal composition comprising the compound of  claim 1 . 
     
     
       7. A polymer comprising a composition of  claim 5 . 
     
     
       8. An optically anisotropic body comprising the polymer of  claim 7 . 
     
     
       9. Resins, resin additives, oils, filters, adhesives, pressure-sensitive adhesives, oils and fats, inks, medicines, cosmetics, detergents, building materials, wrapping materials, liquid crystal materials, organic EL materials, organic semiconductor materials, electronic materials, display elements, electronic devices, communication devices, automotive parts, aircraft parts, machine parts, agricultural chemicals and foods using the compound of  claim 1 , and products using them.